Whether "glamping it" by staying at a B&B, hotel, historic blockhouse, or "roughing it" by bikepacking to the primitive hiker-biker sites along the towpath, a multi-day bike trip in the C&O Canal National Historical Park can be a magical experience for riders of all ages and skill levels.  

One town I highly recommend, whether for a stop for dining or an overnight stay, is Shepherdstown, WV. Located in the lower Shenandoah Valley, it sits adjacent to and across the Potomac River, making it easily accessible from the C&O Canal's towpath.